When I oiled my first set of 800 chips (Trademark "classics"), I did them one at a time with a cloth and it took forever.
When I got my 1000+ Pharoah's, I got them done in almost no time at all. (I received them Friday after work, went to a party, came back and by Saturday morning they were done...and I didn't stay up all night!)
Here's my new approach.
1) Using a large table
2) Lay a towel across the table (beach towels are big)
3) Lay the chips next to each other on the towel
4) Using a small paint roller, put the oil on the roller
5) Roll the chips so that the chips are wet, but not soaked.
6) Repeat 4 & 5 until all chips are oiled.
7) Let them sit for at least 5 minutes (more if you like)

Flip all the chips over
9) Repeat 4 thru 7
Now you have options, using a second towel
1) Wipe the chips down one by one, or
2) Wipe & drag the chips across the towel on the table before doing #1. This is my preferred method. It wipes a lot of oil off before using the "finishing" cloth.
Focus on getting all the oil off the label.
The chips can now be either put away, or layed out for some air drying. As far as I can tell, there's no real difference.
Of note, I found that the outer edges got oiled without having to do anything more. Either the roller touched them and/or the soaking in too care of them.
As I was finishing up, I thought that I should have taken pictures of the process for everyone, but it was too late. It was cool seeing all those chips layed side-by-side...almost better than big stacks...definitely different.
If you have questions about this method, let me know.
Michael